


Fine! I'll try anal! But only on one condition!

by Vincent_Ramone



Category: Panty & Stocking with Garterbelt
Genre: Anal Fingering, Anal Sex, F/M, Femdom, Light Bondage, Oral Sex, Pegging, Rimming
Language: English
Status: Completed
Published: 2020-08-06
Updated: 2020-08-06
Packaged: 2021-03-06 02:14:51
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,335
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25755688
Author URL: https://archiveofourown.org/users/Vincent_Ramone/pseuds/Vincent_Ramone
Summary: Basically a sequel to the other Panty and Stocking fic I wrote. The title itself as well as the tags should hint at what you'll be reading.
Relationships: Anarchy Panty/Briefers "Brief" Rock
Kudos: 17





	Fine! I'll try anal! But only on one condition!

Panty woke up pleasantly sore as well as warm and comfy after her and Brief's first time together. And she felt it many mornings after that because she kept Brief practically strapped to her bed. She really has been training him. Not that either of them would ever complain about that.

He keeps getting laid with the woman of his dreams. A woman who he watched gladly try and succeed to swallow his dick completely. Panty gives incredible head and has an amazing pussy that just milks him for everything. She even brought out costumes, handcuffs, and a paddle on occasion, all for both of them to experience.

The one thing they haven't done despite all the sex and some of the kink play is anal sex. Brief has rimmed her put a finger in but has yet to fuck her there. So while in the kitchen grabbing a snack Brief asked "Hey Panty think we could have sex a little differently tonight?"

Panty grins "Look at you taking initiative what you got in mind high tower?"

Panty doesn't like when he beats around the bush. So he answered to the point.  
"I wanna put it in your ass"

Panty goes wide eyed and yells "With that thing?! It's too huge and I'm way too tight! That'll hurt like fuck!"

"Only if you do it wrong! Not like I'm going to just jam it in! There's supposed to be lube and preparation! Besides you didn't mind it when I ate your ass yesterday!" He defended.

It's amazing what sex can do for your confidence. Brief would have never talked back like this before. Panty grumbled "Yeah?! Well when I rimmed you back you got all moaning and shit too! How bout this?! I get to peg you then you can fuck me right back?!"

"Alright. Cool." Brief says easily

That had her freeze "Wait... What?" She asked slowly

"I'm fine with that. Your tongue felt amazing there and I truly love you Panty. Also you have to have realized that I'm into femdom what with how excited I get when you tie me up or boss me around" Brief clarified very relaxed over the whole situation.

Panty doesn't have an argument to make against that. Also geek boy moaning to the rafters when she rode him when he was tied down spread eagle has a whole new context. It made her start feeling wet the more she thought about it.

Maybe Stocking is onto something with her whole love of bondage and shit. "You got yourself a deal. Now fuck off for a couple hours I got shit to prepare" Panty said then walked off for her sisters room.

Brief stared stupidly for a few moments then registered he's about to probably get bossed around then fucked up the ass by whatever big dildo Panty chooses then get to ride Panty's ass in return.

He tented his jumpsuit with an instantly throbbing erection. He shuffled off to one of the bathrooms for a shower and to help himself prepare. He undressed and turned on the water getting in he gripped his cock and pumped slowly. It certainly isn't the same now that he's had sex. Still nice, but not as satisfying. However when he had a finger circle around his hole he couldn't hold in a moan. It slipped in surprisingly easy. He slowly worked himself open as he kept rubbing himself.

He ended up on his knees he decided to focus on his butt and as two fingers went just a little deeper and brushes what must have been his prostate. The moan that escaped him was different than normal. More pitchy and desperate than his usual sounds.

He got up to three and then even four fingers. He grabbed his swollen penis and rapidly stroked himself as his fingers went deep inside pressing against that special spot. The orgasm he had was also different feeling. Instead of just body jellying and blinding it had the after effect of making him also buzz all over.

He took a minute to just lay back and enjoy the warm water washing over him in his afterglow. His shower was routine after that. Wash his hair and body followed by shaving his pubes and ass.

The red head all clean and in just a towel went to the spare room. He keeps clothes here but didn't bother with any. He's not going to make Panty or himself wait. So now he lays nude half hard and waiting.

Panty had rushed to Stocking for a crash course on all that kinky stuff and hopefully on butt stuff. "Oh the whore finally took the nerds cock out her mouth" Stocking joked having watched Panty burst into her room.

"Look I actually need your help. I agreed to let him put it in my key hole if I could fuck his first. So I need you to explain how a lot of things work in your side of sex real fast" Panty spoke not wanting to play around.

Stocking feels immediately intrigued. "Okay then, so you'll need one of these" Stocking said and then routed through her toys and gave her a strap on harness with a dildo already attached.

"You'll need lube and to slowly stretch him open with your fingers first. Maybe a tongue if you're feeling generous. This advice can also apply to your own ass hole" Stocking said.

Panty nods "okay, can I also borrow some of your ropes? Brief could use a little more variety than the padded cuffs we've been using"

Stocking now feels a little jealous. Bad enough she hears them getting freaky all the time. Now she knows that they are getting more nasty in there than she thought. She also knows what Brief is hiding under his hair she went to tell them to shut up one night and saw his face.

Panty recognized that look "You can have him too ya know? I don't mind sharing because he's just that fucking good. Also if you say be rough get ready I could hardly walk for a few hours and my body was sore for a whole day" she offered

Stocking looked at her in surprise "Would he be okay with that though?" She asked

"Probably. He thinks you're cute too and legitimately enjoys being around you like he does me. If we both ask him nicely it's a done deal as far as I know"

"Thanks sis. I'll hold you to that later. Now remember lube, stretching and a slow entry make it a whole lot less painless. Ooh and here's a how to guide on beginners bondage." Stocking says dumping a bag full of lube ropes and a strap on into Panty's arms.

"And thank you Stocking" Panty gives a conspiratorial grin "There's cameras in my room so I have schlick material for later when I don't have anyone for once. So I'll let you see how this goes later"

Stocking goes wide eyed and a bit red. "Is he cool with that?" She asked curiously

"Yes actually. He found it hot watching himself. Fuck he said as long as I blur his face out I could post it online" Panty answered.

Stocking is definitely touching herself when Panty leaves now. The blonde did leave heading for where she stashed a few of her more sexy outfits. That and she should read some of that how to guide.

Brief jolted a little at the door being kicked open. Panty is dressed in a black pair of short shorts that hug her body tight a fishnet shirt that does not hide her perky tits at all. Brief can definitely see her nipples. She strutted right up to him one of her soft smooth hands lifted his chin.

"Hands and knees slut or your punishment will be heavy" she ordered roughly.

Panty watched him flip right over and his dick swell up immediately. 'damn femdom really does do it for him' she thought.

She brought a hand down smacking his ass. The yelp turned into a moan halfway through. Panty using what knowledge she gained from the guide from earlier had Brief's arms tied behind his back with an end of the rope in Panty's hand for her to yank if she wants.

Brief is a ball of sexual tension he can feel one of Panty's hands alternating between caressing his ass then giving it some decent spanks. "Fuck you got a nice ass. Almost as full as mine. Wonder how much will fit" she purred into his ear.

A spank was followed by the sound of the bottle of lube being opened. Panty grinned because it's strawberry flavored anal lube that Stocking gave her. She apparently had some good insight.

Her first finger slipped right in because of what Brief did earlier. Panty got a grin on her face. "Ooh my cute little nerd played with himself when I was away apparently" she teased slipping a second finger inside.

Brief couldn't hold in his moans. Panty rubbed against his insides with her slim fingers. She slowly stretched him all over again. She pushed right against his bundle of nerves that makes everything buzz all over with electric jolting pleasure.

"Oh Panty!" He yelled after a particularly strong brush against his prostate. Panty giggled and kept purposefully digging into it now up to three fingers. Brief was so red all over his cock leaking pre cum and he is panting so hard.

"Ifhaaa! You kee-fuck! Doing! Shit! Gunna fucking cum!" Brief warned brokenly between moans

Panty pulled her fingers out. Brief lightly gaped open and looked slick with lube. Perfectly open for her toy but before that.  
Brief can feel his cheeks being parted by Panty's hands. He expected to feel the hardness of the dildo that's sure to fuck him. What he did feel was the slick flexible muscle that is Panty's tongue glide over his hole.

High pitched squeals escaped past his lips as Panty laps over his entrance. She circled the ring and dove her tongue right inside and licked his strawberry covered walls. Brief couldn't hold on. A yell of Panty's name his walls clenched around her tongue and he painted the sheets below with a thick white puddle.

His whole body shuddered and his vision went hazy. "Good boy" Panty praised him.

She rubbed his ass almost lovingly and then attached her strap on after some effort and a couple small mutters of fuck when she messed up. She gripped the rope and lightly tugged with one hand, the other on his hip.

The blunt head pressing just so against his entrance. "You ready Brief? I'm about to put it in this tight little fuck hole of yours" Panty speaks with husky excitement in her voice.

"Yes! Fuck me! Please!" Brief ended up begging for it.

Panty slowly pushed in and watches with fascination as the long thick toy was swallowed by Brief's ass hole.

One long drawn out groaning moan sighed past Brief's lips right until Panty's fake dick bottomed out her hips connecting to his cheeks.

"Nhaa! So full" Brief whined.

Panty is so turned on right now. The way the toy rubs against her clit while watching Brief's body shudder only made her drip and feel even better.

It feels so different from his own or Panty's fingers. It is such a stretch and so filling inside him. Panty eventually starts to rock her hips and Brief finds he's very okay with the way the toy rubs against his inner walls.

They both make pleased noises together Panty slowly gaining speed the clap of her hips against Brief's ass an erotic back beat to the song of their voices.

The noises from Brief changed again when Panty started really slamming into him the head of her fake phallus hitting his erotic joy buzzer with each strong smack inside.

A mantra of "Yes!" Started flowing from Brief in clipped high pitched repetition that only gained speed.

Panty took that as good motivation she has both hands on his hips pulling him roughly into her rapidly thrusting hips.

Brief's building coil of orgasm curled tighter and tighter the pressure snapping as his vision went white his ears deaf to his own orgasmic cry.

Panty came right after and her hips eventually stuttered to a stop. Brief had made such a big mess with his second orgasm a thick strand of sticky cum still connected to his rod.

Panty took some with her hand and tasted it. It sent a shiver through her. It had to be one of his thickest and richest loads ever.

"Oh fuck Brief you were amazing!" Panty praised as she pulled out then untied him.

"So, were you, Panty" Brief huffed out blissfully as he tried to catch his breath.

"You definitely earned like two whole times at fucking me in the key hole. Just please tell me you're open to me doing you like this again" Panty says.

"Hell yes! Panty I went momentarily blind because of how good it felt!" Brief agreed enthusiastically.

Panty helped him roll onto his back. Brief smiled so warmly at her she ended up feeling that stupid fluttery feeling in her heart again, whatever the fuck it is.

"You good to still put it in my key hole or do you need a minute?" She asked looking him over.

Brief thinks about it "Maybe after some water and a pain killer first. I feel a little sore now that I'm not singing to the rafters" he answered

Panty got a lewd grin on her face "Want me to kiss it better?" She teased

Brief's dick twitched in interest. Panty knows how much being rimmed turns him on. She also gets turned on herself when playing with a man's ass so win win in her books.

"We can always see and find out" Brief says putting his arms around his legs to hold them up.

Panty put her face right between his cheeks all over again. She licked gently making sure to not put too much pressure or force into it.

It felt a little sensitive but still nice for him. Little by little his member inflated back to its full mast. The red head appreciating the new surge of feel good pumping through him.

"Hey P-panty your t-turn" Brief stuttered  
Although not close he doesn't want to tempt orgasm number three so soon.

Panty pulled away wiping her chin and let him lay flat. She moved and had her dripping cunt hovering over his face. Brief pulled her down to his lips and held her hips tight and ate her pussy out with a passion. "Haaa! Oh shit! Fuck! Wait! For once that's the wrong hole!" She shouted and moaned.

Brief slurped her juices and swallows. She always tasted good to him. He kept at it for a few short moments before releasing her. "Couldn't resist, now turn around so I can have a better angle" Brief said.

She did and Brief had her cheeks spread and was tonguing her ass immediately.  
"Damn! Why do you have to be so good with your mouth?!" Panty praised.

She's had some enthusiastic partners before but none of them ever made out with her holes especially her back door like this. He lapped, sucked, and circled her hole and wriggled his tongue deep inside. "It's so good! MMM fuck yeah! Make out with my ass hole!" Panty ordered grinding down on his face.

Brief is being nearly suffocated but he barely cares as he buries his face between her pale plump cheeks tongue fucking her with a passion. He gently pushed on her ass to signal for her to get up.

She did and was on her hands and knees looking back at him expectantly. Brief found the lube and coated his fingers.  
Thanks to the rimjob the first slipped in a bit easier. Brief was slow, methodical and used his spare hand to rub her pussy at the same time.

As the fingers increased Panty's enjoyment of having something in there did too. Brief filled her in what she's now going to say is the right way for butt stuff.  
"How many fingers are in you? Do you know?" Brief asked

Purring the words right into her ear as the digits separated to stretch her even more open. "Hafuuuck! Thr-three?!" She groaned her answer 

"Four" Brief corrected and then slid his fingers out then flipped her onto her back.  
She watched him pour the lube onto his absolutely throbbing cock. He pulled her by the hips then trailed his hands down her legs. He lifted them and the blunt spongy head of his erection touched the opening of her key hole.

"Let's see if I can give you a nice pair of bunny ears as I drill this tight slutty ass of yours"

Panty shuddered from his words. She taught him well when it comes to dirty talk for sure. The head popped right in after just a small amount of pressure and Brief was welcomed into the tight soft heat of Panty's back door.

They both moan and groan as Brief slowly inches his thick long rod in. Panty already feels so full and stretched and she hasn't even taken all of it yet. Also she can't help but admire his patience. He stops every inch let's her adjust and then slowly pulls back and adds another piece of himself.

The heavy weight of him inside touched something deep as his hips finally connected to her ass. She is almost certain she can feel him in her stomach.  
The burning stretch actually feeling good.

"Start, moving" Panty slowly said.

Brief slowly started thrusting. Rocking his hips in a gentle rhythm watching with fascination as his penis disappeared into her tightest hole.

Panty thinks this may become her favorite new place to get fucked. It's such a different kind of fullness and pleasure than being screwed the normal way. What she wants to know is what cumming is going to feel like.

"Faster! Haa! I Wanna be fucked hard! Panty ordered.

Brief gulped but nodded his pace picking up. He really did end up folding her till her legs were beside her head and passionately slammed into her. His hips and balls slapping her cheeks pressing his weight into it.

Just like any other time she started getting close to finishing the blonde's moans and noises got loud.

Hooooh! Yeeees!" She screamed as she came. She squirted painting her and Brief her body clamping down around him sending the red head to his own orgasm.

His cum pumped in thick heavy ropes cock pulsing and throbbing as it spewed.  
The hot rush of semen painting her insides white Panty groaned and cooed at being creampied.

Brief rolled his hips to a gradual stop and caught his breath before pulling out.  
"We're doing that again! Oh damn that was a good O!" She says with a very pleased smile.

Brief smiled back "I'm glad you liked that too. Looks like we both have something new we like"

Panty jolted "Ah that reminds me, Stocking would love a turn and I would be okay with that. Talent like yours should be shared"

Her words surprised him. "W-w-w-what?! I, I don't kn-know what t-to say a-b-b-b-bout that!" He stuttered

"I would probably start with "fuck yeah two hot chicks want me. And the one I'm already fucking is cool with it!" But that's just me. So sometime later if you want to have the threesome of your life just say the word" Panty responded

"That and we're sisters so that's one for the kink list to remember" she added.

Brief did his best impression of a giant strawberry and went all quiet for a few moments. "If both of you are okay with it and that's what she really wants" he nearly whispered.

Oh Panty has big plans now.


End file.
